1. Sad Satan Video Game

You may only be familiar with the idea of the deep web through the many news reports about it (most of which make it sound like a place that exists solely for people to connect with strangers who want to help them commit acts of organized crime). But there's much more to it than all the think pieces and crime procedural TV shows might have led you to believe.
All kinds of things exist in the password-protected depths of the deep web — including disturbing video games, like the mysterious "Sad Satan," which was supposedly found on a deep web forum. A user of that forum found it and sent it to Jamie Farrell, of the "Obscure Horror Corner" YouTube channel. Farrell uploaded some videos of the disturbing survival horror game, which involves long walks down darkened hallways, garbled-sounding backwards voices and a photo of a guy wearing deer antlers. Then, after claiming that the video was installing programs on his computer without his permission, Farrell deleted the game file...and no one has been able to find the actual game since.

2. I Feel Fantastic

I Feel Fantastic was posted to YouTube in 2009 by user Creepyblog. The video itself is pretty straight forward; a mannequin like animatronic character named Tara moves her head and arms while singing the song “I Feel Fantastic.” While that’s creepy enough in itself, the strangeness takes a new turn when seemingly unrelated footage begins to intercut Tara’s poses. The footage, possibly of a backyard, zooms in on a pile of sticks while the lyrics say “Run, run, run.”

3. The Max Headroom Hack

The now infamous hack featured an unidentified individual wearing a mask resembling the fictional character Max Headroom. The pre-recorded video was seen twice in the span of three hours after hackers were able to infiltrate a broadcast signal for WTTW and interrupted an episode of Doctor Who on 22nd November 1987. The masked character bounced around the screen maniacally to a swirling metallic background before the intrusion cut off. While the hijacking itself was unsettling, the lack of obvious motive or message to the video made it difficult to pinpoint who possible suspects might be. Despite a full investigation, the perpetrators were never caught and the Max Headroom hack has since become the stuff of legend.
A few hours later, folks in the same area who were trying to watch a Doctor Who episode on PBS got a longer version of the video that news viewers saw before: in this later version, the man in the rubber mask mumbles a bunch of nonsense for a minute and a half and then, at the videos' climax, is spanked by a woman with a flyswatter.

4. The Plague Doctor

The black and white segment comes in at two minutes in length and features someone dressed as a plague doctor. The outfit was designed to keep airborne illness from infecting those treating victims from various diseases. It includes a long dark beak-like mask with black shroud that covers the wearer’s entire body.
The Plague Doctor Video was first published on the Swedish blog GadgetZZ in 2015. The video depicts a person in a plague doctor’s mask doing some very strange things in an apparently abandoned building. Morse code, an odd static tone, and some jump-cuts and overlays of mutilated bodies spliced in all feature in this deeply unsettling video. The editor of GadgetZZ claimed the video was sent to him as part of a digital puzzle contained on a DVD delivered to his house with no return address. Not knowing what else what to do with it, he posted it on his website. YouTube user AETBX also posted the video online, claiming to have received the video anonymously in the mail. His video was entitled ‘01101101 01110101 01100101 01110010 01110100 01100101’ which in binary code this translates to “Muerte”, the Spanish word for death.

5. Blank Room Soup

This video is also thought to have emerged from the Deep Web. At
first glance, the video seems relatively tame. There is a man sitting at
a table with his eyes blacked out and eating soup. A person in a
character costume comes up behind him and begins patting him on the
back. As this happens, the man eating begins to sob. Then a second
person dressed in the same getup enters the frame and appears to be
trying to comfort the now crying man.
When it was first uploaded in 2008, it was taken as a joke, prank or
some kind of strange experiment. It’s been nearly nine years since its
appearance on the web, and still no one has stepped forth to claim
it—which has led some to believe that there may be a more sinister story
behind the video than what was initially thought.